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제118회 대한화학회 학술발표회, 총회 및 기기전시회 안내 New concise total syntheses of (-)-neocosmosin A and ent-(-)-monocillin IV via Intramolecular Diels-Alder reaction of 2-pyrone [우수포스터상]

2016년 9월 2일 11시 52분 01초
ORGN.P-447 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
10월 14일 (금요일) 11:00~12:30
저자 및
이준호, 조천규*
한양대학교 화학과, Korea
Resorcyclic acid lactones (RALs) are polyketide-derived benzannulated macrolides, named for their -resorcyclate core structure fused to a 12- or 14-membered lactone ring. Many of them exhibit intriguing biological activities that include anticarcinogenic, antimalarial, antifungal, and antibiotic properties. Several RAL compounds are in fact currently under development for the clinical applications. Because of their potential values as new drug candidates, invention of methods and/or routes that allow rapid and divergent synthesis of RALs would be of significant interest. Neocosmosin A is a recently found RAL, co-isolated with neocosmosin B and C from a fungus Neocosmospora sp. (UM-031509) in 2012. It was shown to have a strong binding affinity for human opioid and cannabinoid receptors.
As a part of our ongoing study on 3,5-dibromo-2-pyrone toward target oriented synthesis, we have devised A new synthetic route to (-)-neocosmosin A and ent-(-)-monocillin IV were devised through the elaboration of intramolecular Diels-Alder cycloaddition of 2-pyrone containing bromo-propiolate group as dienophile. The IMDA reaction was accompanied with cycloreversion of carbon dioxide to give benzannulated macrolide with two bromide groups at C14 and C16. Installation of the pinacolboryl groups and oxidations allowed the total syntheses of neocosmosin A and ent-monocillin IV.